A1 Journal article (refereed)
Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes (2020)

Taimoory, S. M., Twum, K., Dashti, M. A. P., Lahtinen, M., Rissanen, K., Puttreddy, R., Trant, J. F., & Beyeh, N. K. (2020). Bringing a Molecular Plus One : Synergistic Binding Creates Guest-Mediated Three-Component Complexes. Journal of Organic Chemistry, 85(9), 5884-5894. https://doi.org/10.1021/acs.joc.0c00220

JYU authors or editors

Publication details

All authors or editors: Taimoory, S. Maryamdokht; Twum, Kwaku; Dashti, Mohadeseh and Pan, FangFang; Lahtinen, Manu; Rissanen, Kari; Puttreddy, Rakesh; Trant, John F.; Beyeh, Ngong Kodiah

Journal or series: Journal of Organic Chemistry

ISSN: 0022-3263

eISSN: 1520-6904

Publication year: 2020

Volume: 85

Issue number: 9

Pages range: 5884-5894

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.joc.0c00220

Publication open access: Not open

Publication channel open access: 

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/68204

Abstract

C-Ethyl-2-Methylresorcinarene (A), pyridine (B), and a set of ten carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple non-covalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution as explored by both experimental and computational methods. The interactions be-tween A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions between A and B, demonstrating positive cooperativity. Our results reveal that the two-component system such as that formed by A and B can form the basis for the development of specific sensors for the molecular recognition of carboxylic acids.

Keywords: carboxylic acids; molecules; recognition; supramolecular chemistry

Free keywords: carboxylic acids; molecular recognition; supramolecular chemistry; diagnostic tools

Contributing organizations

Related projects

Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 2